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π-Facial selectivities in nucleophilic additions to 4-hetero-tricyclo[5.2.1.02,6]decan-10-ones and 4-hetero-tricyclo[5.2.1.02,6]dec-8-en-10-ones: an experimental and computational study

✍ Scribed by Goverdhan Mehta; Vanessa Gagliardini; U.Deva Priyakumar; G.Narahari Sastry


Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
66 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis


6

]decan-10-ones and endo-tricyclo [5.2.1.0 2,6 ]dec-8-en-10-ones with hetero atom modifications at the distal C-4 position have been subjected to hydride reduction. p-Face selectivities in these systems are largely governed by the same electronic factors that were earlier identified in the case of the norbornyl system. A computational study demonstrates good predictability at the semi-empirical level.